Methyl bromoacetate → HCID 45091085, compound

HRID 1251465Notes

Reaction equation

HRID 1251465 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.Br[CH2:9][C:10]([O:12][CH3:13])=[O:11]>CN(C=O)C.[Ag]=O>[N:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[O:1][CH2:9][C:10]([O:12][CH3:13])=[O:11]

Participants

5

Reactant 2

HCID 60984Methyl bromoacetateHCID 178516071HCID 178516071, compound

Product 1

HCID 45091085HCID 45091085, compoundYield 11.4%

Reagents, catalysts & solvents 2

HCID 92152Silver(II) oxideCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-hydroxypyridine(5 g) in DMF(150 ml) was added silver oxide (I) (24 g) and methyl bromoacetate(20 g) and stirred at room temperature for 2 hours. After the catalyst was filtered off through celite, the filtrate was evaporated. The residue was dissolved in ethyl acetate and the solution was washed with brine, dried(MgSO4) and evaporated to dryness. The residue was purified by column chromatography on silica gel (chloroform: methanol=100:1) to obtain methyl 2-(2-pyridyloxy)acetate(1.0 g). According to the same manner as described above, the title compound was synthesized (0.1 g). m.p. 110° C.

Workup

  1. filtrationAfter the catalyst was filtered off through celite
  2. customthe filtrate was evaporated
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washthe solution was washed with brine, dried(MgSO4)
  5. customevaporated to dryness
  6. customThe residue was purified by column chromatography on silica gel (chloroform: methanol=100:1)

Sources & evidence

ORD record
ord-4be03364916946978b9802a981811647
Source dataset
uspto-grants-2002_01
Patent number
US06342516B1

Reaction notes

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